EFFICIENT SYNTHESIS AND ANTICANCER ACTIVITIES OF SOME NOVEL FUNCTIONALIZED (4-OXO-4H-CHROMEN-3-YL)2-SELENOXO-1,2-DIHYDROPYRIMIDINES

被引:2
作者
Ali, Tarik E. [1 ,2 ]
Assiri, Mohammed A. [1 ]
Ali, Mamdouh M. [3 ]
Ali, Abeer E. M. [3 ]
Yahia, Ibrahim S. [4 ,5 ,6 ]
Zahran, Heba Y. [4 ,5 ,6 ]
机构
[1] King Khalid Univ, Fac Sci, Dept Chem, Abha, Saudi Arabia
[2] Ain Shams Univ, Fac Educ, Dept Chem, Cairo, Egypt
[3] Natl Res Ctr, Genet Engn & Biotechnol Div, Biochem Dept, Giza, Egypt
[4] King Khalid Univ, Res Ctr Adv Mat Sci RCAMS, Abha, Saudi Arabia
[5] King Khalid Univ, Fac Sci, Dept Phys, Abha, Saudi Arabia
[6] Ain Shams Univ, Fac Educ, Dept Phys, Cairo, Egypt
关键词
Chromone; Selenium; Pyrimidine; Anticancer Activity; CHROMONES; APOPTOSIS; ANTIOXIDANT; CATALYST; CELLS;
D O I
10.3987/COM-20-14324
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Some novel functionalized 2-selenoxo-1,2-dihydropyrimidines bearing a chromone ring 2a-h were synthesized in excellent yields via a simple one-pot reaction. The simple method depended on one-pot three-component the reaction of 3-formylchromone (1) and selenourea with some active methylene compounds in the presence of sodium benzoate as a basic catalyst in a mixture of ethanol and water. The reactions were completed in 1.5-2.5 h in 88-94% yields. Structures of the synthesized compounds were based on elemental analysis, IR, H-1- and C-13-NMR and mass spectrometry. The anticancer properties of the synthesized compounds were evaluated against five cancer cell lines. Compounds 2a-d displayed the most potent anticancer activities against A549, MCF-7 and HepG2 cell lines in comparison with doxorubicin as the standard drug.
引用
收藏
页码:1831 / 1844
页数:14
相关论文
共 42 条
[1]   2-(4-methylphenyl)-1,3-selenazol-4-one induces apoptosis by different mechanisms in SKOV3 and HL 60 cells [J].
Ahn, Hak Jun ;
Koketsu, Mamoru ;
Yang, Eun Mi ;
Kim, Yong Man ;
Ishihara, Hideharu ;
Yang, Hyun Ok .
JOURNAL OF CELLULAR BIOCHEMISTRY, 2006, 99 (03) :807-815
[2]  
Ali M. M., 2014, ASIAN J PHARM CLIN R, V7, P168
[3]   FIRST SYNTHESIS OF BENZO [e] [1,3,2]DIAZAPHOSPHININO[1,6-c]-[1,3,2]OXAZAPHOSPHININES [J].
Ali, Tarik E. ;
Assiri, Mohammed A. ;
Yahia, Ibrahim S. .
HETEROCYCLES, 2019, 98 (09) :1265-1272
[4]   REACTION OF 2-IMINO-2H-CHROMENE-3-CARBOXAMIDE WITH PHOSPHORUS HALIDES: SYNTHESIS OF SOME NOVEL CHROMENO[2,3-d][1,3,2]DIAZAPHOSPHININES AND CHROMENO[4,3-c][1,2]-AZAPHOSPHOLE AND THEIR ANTIOXIDANT AND CYTOTOXICITY PROPERTIES [J].
Ali, Tarik E. ;
Assiri, Mohammed A. ;
El-Shaaer, Hafez M. ;
Fouda, Ahmed M. ;
Hassan, Mohamed M. ;
Hassanin, Noha M. .
HETEROCYCLES, 2019, 98 (05) :681-692
[5]   Novel pyrimidinic selenourea induces DNA damage, cell cycle arrest, and apoptosis in human breast carcinoma [J].
Barbosa, Flavio A. R. ;
Siminski, Tamila ;
Canto, Romulo F. S. ;
Almeida, Gabriela M. ;
Mota, Nadia S. R. S. ;
Ourique, Fabiana ;
Pedrosa, Rozangela Curi ;
Braga, Antonio Luiz .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2018, 155 :503-515
[6]   1,3-Selenazole [J].
Below, H ;
Pfeiffer, WD ;
Geisler, K ;
Lalk, M ;
Langer, P .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (17) :3637-3639
[7]   Functional Mimics of Glutathione Peroxidase: Bioinspired Synthetic Antioxidants [J].
Bhabak, Krishna P. ;
Mugesh, Govindasamy .
ACCOUNTS OF CHEMICAL RESEARCH, 2010, 43 (11) :1408-1419
[8]  
Block E, 1998, PHOSPHORUS SULFUR, V136, P1
[9]   Synthesis of 4-aryl-2-imino-2H-selenazolines by a reaction of α-(selenocyanato)acetophenones with anilines [J].
Bodtke, Anja ;
Kandt, Madeleine ;
Pfeiffer, Wolf-Diethard ;
Langer, Peter .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2007, 182 (01) :209-217
[10]   What is a green solvent?: A comprehensive framework for the environmental assessment of solvents [J].
Capello, Christian ;
Fischer, Ulrich ;
Hungerbuehler, Konrad .
GREEN CHEMISTRY, 2007, 9 (09) :927-934